CN103980314B - Compound containing multiple active group and preparation method thereof - Google Patents
Compound containing multiple active group and preparation method thereof Download PDFInfo
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- CN103980314B CN103980314B CN201410224366.7A CN201410224366A CN103980314B CN 103980314 B CN103980314 B CN 103980314B CN 201410224366 A CN201410224366 A CN 201410224366A CN 103980314 B CN103980314 B CN 103980314B
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Abstract
The present invention relates to a kind of response type phosphorus-nitrogen combustion inhibitor, specifically a kind of compound containing multiple active group and preparation method thereof, (1) takes cyanuric chloride and is dissolved in the first solvent, be stirred to and dissolve completely, slowly be warming up to 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed; (2) under nitrogen protection atmosphere, add the phosphorous acid ester solution be dissolved in the first solvent, reaction 4 ~ 6h, keep in reaction process stirring.Compound Phase containing multiple active group of the present invention has following beneficial effect for prior art: described compound be with cyanuric chloride, phosphite ester compound (trimethyl phosphite or triethyl-phosphite), containing the multicomponent alcoholics compound (neopentyl glycol, glycerol or tetramethylolmethane) of quaternary carbon (or secondary carbon) atom for raw material, be prepared from by Michaelis-Arbuzov electrophilic addition reaction and nucleophilic substitution reaction.
Description
Technical field
The present invention relates to a kind of response type phosphorus-nitrogen combustion inhibitor, specifically a kind of compound containing multiple active group and preparation method thereof.
Background technology
Along with the development of Materials science, synthesized polymer material is widely used in various field, has very large impact to the productive life of people.But most of organic material all has incendive feature, according to incompletely statistics, China's presence of fire in 2012 reaches 110,000 more than.In face of the fire of high risk like this, research material flame-retarded technology is very urgent.
Reactive flame retardant is the fire retardant that a class contains sp act functional group, it introduces fire-retardant group in the mode of chemical bonding in macromolecular material, can be evenly distributed in polymer molecular chain with the form of molecule, therefore, flame retarding efficiency is high, only need the flame retardant resistance that just effectively can improve material on a small quantity, stop material ignited and suppress flame transmission, make body material have more lasting flame retardant effect.
For single active group reactive flame retardant, multi-active base group fire retardant contains multiple reaction active groups, during with polymer-bound, has relatively high percentage of grafting, fundamentally can improve the flame retardant properties of material.In addition, to have ignition-proof element content high for multi-active base group reactive flame retardant, the feature of thermostability, weather resistance, good flame retardation effect, is therefore the excellent char-forming agent of fire retardant material.In addition, multi-active base group's phosphor-nitrogen expansion type combustion inhibitor has relatively low price and environmentally friendly feature relative to other fire retardants, on also less by the impact of flame-retardant polymer physicals, response type phosphor nitrogen combustion inhibitor containing multiple active group is applied in material, the flame retardant properties of material can be made fundamentally to be improved, compared to the fire retardant containing single active group, fire retardant containing multiple active group has plurality of advantages, thus becomes the development trend of following flame retardant area just gradually.
Summary of the invention
The problem that reaction active groups is relatively less, amount of flame-retardant agent is more that the present invention has to solve conventional reactive flame retardant at present, provides a kind of compound containing multiple active group and preparation method thereof.
The present invention is achieved by the following technical solutions: the compound containing multiple active group, and its structural formula is:
In formula: R is-CH
3or-CH
2cH
3;
n=5，m=2；
Or n=4, m=3;
Or n=5, m=4.
Concrete molecular structure is:
。
Its synthetic route is as follows:
。
The concrete steps of preparation method's (synthetic route) of the described compound containing multiple active group are:
(1) take cyanuric chloride to be dissolved in the first solvent, be stirred to and dissolve completely, be slowly warming up to 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(2) under nitrogen protection atmosphere, add the phosphorous acid ester solution be dissolved in the first solvent, reaction 4 ~ 6h, keep in reaction process stirring;
Described phosphorous acid ester is trimethyl phosphite or triethyl-phosphite;
(3) after question response terminates, stop insulation, be cooled to room temperature gradually, filter, revolve steaming, obtain intermediate M;
Described first solvent is toluene, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane or the mixed solvent of toluene and acetone;
Second step,
(4) intermediate M is dissolved in the second solvent, is stirred to and dissolves completely, be slowly warming up to 40 ~ 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(5) take polyvalent alcohol and acid binding agent is dissolved in the second solvent, be stirred to and dissolve completely, be added dropwise in the second solvent containing intermediate M, insulation reaction 7 ~ 9h; After having reacted, refrigeration leaves standstill 10h, filters the hydrochloride of acid binding agent, revolves and steams except desolventizing, obtain yellow oily liquid, be the compound containing multiple active group;
Described second solvent is tetrahydrofuran (THF) or Isosorbide-5-Nitrae-dioxane, and polyvalent alcohol is neopentyl glycol, glycerol or tetramethylolmethane, and acid binding agent is triethylamine, diisopropylethylamine or pyridine.
Solvent in the first step of the present invention and second step is to make reactants dissolved, and its add-on is manageable for those skilled in the art hold.
In second step, adding of acid binding agent is hydrogenchloride in order to produce in neutralization reaction process, and it does not participate in compound reaction and generates, and its add-on is manageable for those skilled in the art hold.
Further, the yellow oily liquid that step (5) obtains, with acetone solution, together with quality is stirred in silica-gel powder, normal temperature ventilation is dried, with the ethyl acetate of 1:20 volume ratio and sherwood oil for eluent, carry out silica gel column chromatography separating-purifying, obtain the yellow oily liquid after purifying.The compound containing multiple active group after above-mentioned steps process, its purity is higher.
Compound Phase containing multiple active group of the present invention has following beneficial effect for prior art: described compound be with cyanuric chloride, phosphite ester compound (trimethyl phosphite or triethyl-phosphite), containing the multicomponent alcoholics compound (neopentyl glycol, glycerol or tetramethylolmethane) of quaternary carbon (or secondary carbon) atom for raw material, be prepared from by Michaelis-Arbuzov electrophilic addition reaction and nucleophilic substitution reaction; Described compound contains multiple active reactive group, integrates carbon source, acid source, source of the gas, has phosphorus-nitrogen cooperative flame retardant effect; Especially this compound contains multiple reaction active groups---chlorine atom (Cl), stable covalent linkage can be formed with the related activity group generation chemical reaction in multiple polymers matrix, thus give flame-retardant polymer high thermostability, good one-tenth carbon performance, and can give polymkeric substance excellent flame retardant properties when less fire retardant addition.Synthesis technique of the present invention is simple, and the prices of raw and semifnished materials are cheap; Temperature of reaction is low, and energy consumption is little; Synthesis required equipment is simple, easy to operate, is applicable to various containing OH, NH
2, COOH isoreactivity group the fire-retardant finish of polymeric matrix.
Accompanying drawing explanation
Fig. 1 is the Fourier transform infrared spectroscopy spectrogram of FR-1 described in embodiment 1.
Fig. 2 is the proton nmr spectra spectrogram of FR-1 described in embodiment 1.
Fig. 3 is the Fourier transform infrared spectroscopy spectrogram of FR-2 described in embodiment 3.
Fig. 4 is the proton nmr spectra spectrogram of FR-2 described in embodiment 3.
Fig. 5 is the Fourier transform infrared spectroscopy spectrogram of FR-3 described in embodiment 5.
Fig. 6 is the proton nmr spectra spectrogram of FR-3 described in embodiment 5.
Embodiment
embodiment 1
The preparation method of the described compound (FR-1) containing multiple active group,
The steps include:
The first step,
(1) 5.52g(0.03mol is taken) cyanuric chloride is dissolved in 50mL toluene, is stirred to and dissolves completely, be slowly warming up to 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(2) under nitrogen protection atmosphere, the 5.48g(0.033mol be dissolved in 50mL acetone is added) triethyl-phosphite solution, reaction 4h, keeps in reaction process stirring;
(3) after question response terminates, stop insulation, be cooled to room temperature gradually, filter, revolve steaming, obtain intermediate M;
Second step,
(4) by 5.72g(0.02mol) intermediate M is dissolved in 50mL tetrahydrofuran (THF), is stirred to and dissolves completely, be slowly warming up to 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(5) 1.04g(0.01mol is taken) neopentyl glycol and triethylamine be dissolved in 50mL tetrahydrofuran (THF), be stirred to and dissolve completely, be added dropwise in the tetrahydrofuran (THF) containing intermediate M, insulation reaction 8h; After having reacted, refrigeration leaves standstill 10h, filters the hydrochloride of triethylamine, revolves and steams except desolventizing, obtain yellow oily liquid, be the compound containing multiple active group;
The 3g yellow oily liquid that step (5) obtains, with acetone solution, together with being stirred in silica-gel powder etc. quality, normal temperature ventilation is dried, with the ethyl acetate of 1:20 volume ratio and sherwood oil for eluent, carry out silica gel column chromatography separating-purifying, obtain the yellow oily liquid 2.52g after purifying, productive rate is 83.9%.
As seen from Figure 1, for FR-1,784cm
-1it is the C-Cl infrared absorption peak of triazine ring; 1022cm
-1for the stretching vibration peak of=C-O-C-structure; 1063cm
-1place is the C-N stretching vibration peak of triazine ring, and the position of the stretching vibration peak of C=N is at 1468cm
-1place; 1161cm
-1the infrared absorption peak at place is the absorption peak of the P-O of phosphate ester structure; 1230cm
-1it is the stretching vibration peak of P=O; 1468cm
-1the peak value at place is that triazine structure is connected with phosphate ester structure=the stretching vibration peak of C-P; 1574cm
-1place is the stretching vibration peak of C-O-P structure.The generation of=C-O-C-and=C-P structure shows that FR-1 is successfully synthesized.As seen from Figure 2,
1h-NMR (600MHz, DMSO-
d 6 , TMS): δ 1.22 (
s,
3H, CH
3), 1.16 (
t,
j=6.6Hz, 12H, 4CH
3), 2.51 (
s,
h, DMSO), 3.49 (
q,J=6.6Hz, 8H, 4OCH
2) ppm, these data show that there is FR-1 in this molecular structure is successfully synthesized.
embodiment 2
The preparation method of the described compound (FR-1) containing multiple active group,
The steps include:
The first step,
(1) 9.30g(0.05mol is taken) cyanuric chloride is dissolved in 80mL acetone, is stirred to and dissolves completely, be slowly warming up to 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(2) under nitrogen protection atmosphere, the 6.20g(0.05mol in the mixed solvent (volume ratio is 1:2) being dissolved in 80mL toluene and acetone is added) trimethyl phosphite solution, reaction 6h, keeps in reaction process stirring;
(3) after question response terminates, stop insulation, be cooled to room temperature gradually, filter, revolve steaming, obtain intermediate M;
Second step,
(4) by 9.76g(0.04mol) intermediate M is dissolved in 80mL1, and in 4-dioxane, be stirred to and dissolve completely, be slowly warming up to 55 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(5) 2.08g(0.02mol is taken) neopentyl glycol and diisopropylethylamine be dissolved in 80mL1, and in 4-dioxane, be stirred to and dissolve completely, be added dropwise in the Isosorbide-5-Nitrae-dioxane containing intermediate M, insulation reaction 7h; After having reacted, refrigeration leaves standstill 10h, filters the hydrochloride of diisopropylethylamine, revolves and steams except desolventizing, obtain yellow oily liquid, be the compound containing multiple active group;
The 3.5g yellow oily liquid that step (5) obtains, with acetone solution, together with being stirred in silica-gel powder etc. quality, normal temperature ventilation is dried, with the ethyl acetate of 1:20 volume ratio and sherwood oil for eluent, carry out silica gel column chromatography separating-purifying, obtain the yellow oily liquid 2.84g after purifying, productive rate is 81.2%.
embodiment 3
The preparation method of the described compound (FR-2) containing multiple active group,
The steps include:
The first step,
(1) 7.44g(0.04mol is taken) cyanuric chloride is dissolved in 70mL1, and in 4-dioxane, be stirred to and dissolve completely, be slowly warming up to 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(2) under nitrogen protection atmosphere, add and be dissolved in 50mL1, the 7.30g(0.044mol in 4-dioxane) triethyl-phosphite solution, reaction 5h, keeps in reaction process stirring;
(3) after question response terminates, stop insulation, be cooled to room temperature gradually, filter, revolve steaming, obtain intermediate M;
Second step,
(4) by 8.58g(0.03mol) intermediate M is dissolved in 70mL tetrahydrofuran (THF), is stirred to and dissolves completely, be slowly warming up to 40 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(5) 0.92g(0.01mol is taken) glycerol and pyridine be dissolved in 50mL1, and in 4-dioxane, be stirred to and dissolve completely, be added dropwise in the tetrahydrofuran (THF) containing intermediate M, insulation reaction 9h; After having reacted, refrigeration leaves standstill 10h, filters the hydrochloride of pyridine, revolves and steams except desolventizing, obtain yellow oily liquid, be the compound containing multiple active group;
The 3g yellow oily liquid that step (5) obtains, with acetone solution, together with being stirred in silica-gel powder etc. quality, normal temperature ventilation is dried, with the ethyl acetate of 1:20 volume ratio and sherwood oil for eluent, carry out silica gel column chromatography separating-purifying, obtain the yellow oily liquid 2.23g after purifying, productive rate is 76.3%.
As seen from Figure 3,846cm
-1it is the characteristic signal peak of tr-Cl; 1028cm
-1the infrared absorption peak at place is that triazine ring is connected with glycerol=the stretching vibration peak of C-O-C-structure; 1160cm
-1the peak value at place is the characteristic peak of the P-O of triazine ring and phosphonic acid ester structure; 1217cm
-1triazine ring is connected with phosphonic acid ester structure=characteristic peak of C-P; 1467cm
-1it is the infrared absorption peak of phosphonic acid ester P=O; 1580cm
-1it is the characteristic peak of triazine ring C=N structure; 2967cm
-1phosphonic acid ester structure-CH
3or-CH
2the stretching vibration of-structure.The generation of=C-O-C-structure ,=C-P structure, shows that FR-2 has successfully been synthesized.As seen from Figure 4,
1h-NMR (600MHz, DMSO-
d 6 , TMS): δ 1.39 (
t,
j=6.6Hz,
18H, 6CH
3), 2.51 (
s,
h, DMSO), 3.43 (
s,
4H, 2CH
2), 3.51 (
s,
h, CH), 3.62 (
q,
12H, 6CH
2) ppm.These data show that there is FR-2 in this molecular structure is successfully synthesized.
embodiment 4
The preparation method of the described compound (FR-2) containing multiple active group,
The steps include:
The first step,
(1) 7.44g(0.04mol is taken) cyanuric chloride is dissolved in 70mL tetrahydrofuran (THF), is stirred to and dissolves completely, be slowly warming up to 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(2) under nitrogen protection atmosphere, the 4.96g(0.04mol be dissolved in 70mL toluene is added) trimethyl phosphite solution, reaction 5h, keeps in reaction process stirring;
(3) after question response terminates, stop insulation, be cooled to room temperature gradually, filter, revolve steaming, obtain intermediate M;
Second step,
(4) by 7.32g(0.03mol) intermediate M is dissolved in 70mL1, and in 4-dioxane, be stirred to and dissolve completely, be slowly warming up to 50 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(5) 0.92g(0.01mol is taken) glycerol and triethylamine be dissolved in 50mL tetrahydrofuran (THF), be stirred to and dissolve completely, be added dropwise in the Isosorbide-5-Nitrae-dioxane containing intermediate M, insulation reaction 7h; After having reacted, refrigeration leaves standstill 10h, filters the hydrochloride of triethylamine, revolves and steams except desolventizing, obtain yellow oily liquid, be the compound containing multiple active group;
The 3g yellow oily liquid that step (5) obtains, with acetone solution, together with being stirred in silica-gel powder etc. quality, normal temperature ventilation is dried, with the ethyl acetate of 1:20 volume ratio and sherwood oil for eluent, carry out silica gel column chromatography separating-purifying, obtain the yellow oily liquid 2.20g after purifying, productive rate is 73.5%.
embodiment 5
The preparation method of the described compound (FR-3) containing multiple active group,
The steps include:
The first step,
(1) 9.30g(0.05mol is taken) cyanuric chloride is dissolved in the mixed solvent (volume ratio is 2:1) of 80mL toluene and acetone, is stirred to and dissolves completely, be slowly warming up to 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(2) under nitrogen protection atmosphere, the 9.13g(0.055mol be dissolved in 70mL tetrahydrofuran (THF) is added) triethyl-phosphite solution, reaction 6h, keeps in reaction process stirring;
(3) after question response terminates, stop insulation, be cooled to room temperature gradually, filter, revolve steaming, obtain intermediate M;
Second step,
(4) by 11.44g(0.04mol) intermediate M is dissolved in 80mL1, and in 4-dioxane, be stirred to and dissolve completely, be slowly warming up to 45 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(5) 1.36g(0.01mol is taken) tetramethylolmethane and diisopropylethylamine be dissolved in 70mL tetrahydrofuran (THF), be stirred to and dissolve completely, be added dropwise in the Isosorbide-5-Nitrae-dioxane containing intermediate M, insulation reaction 8h; After having reacted, refrigeration leaves standstill 10h, filters the hydrochloride of diisopropylethylamine, revolves and steams except desolventizing, obtain yellow oily liquid, be the compound containing multiple active group;
The 3g yellow oily liquid that step (5) obtains, with acetone solution, together with being stirred in silica-gel powder etc. quality, normal temperature ventilation is dried, with the ethyl acetate of 1:20 volume ratio and sherwood oil for eluent, carry out silica gel column chromatography separating-purifying, obtain the yellow oily liquid 2.03g after purifying, productive rate is 67.5%.
As seen from Figure 5,837cm
-1it is the characteristic signal peak of tr-Cl; 1056cm
-1the infrared absorption peak at place is that triazine ring is connected with tetramethylolmethane=the stretching vibration peak of C-O-C-structure; 1161cm
-1the peak value at place is the characteristic peak of the P-O of triazine ring and phosphonic acid ester structure; 1228cm
-1triazine ring is connected with phosphonic acid ester structure=characteristic peak of C-P; 1469cm
-1it is the infrared absorption peak of phosphonic acid ester P=O; 1560cm
-1it is the characteristic peak of triazine ring C=N structure; 2921cm
-1phosphonic acid ester structure-CH
3or-CH
2-structure stretching vibration peak.The generation of=C-O-C-structure ,=C-P structure, shows that FR-3 has successfully been synthesized.As seen from Figure 6,
1h-NMR (600MHz, DMSO-
d 6 , TMS): δ 1.15 (
t,
j=6.6Hz,
24H, 8CH
3), 3.46 (
q,
16H, 8-CH
2-), 4.76 (
m,
8H, 4OCH
2) ppm, wherein 1.20,1.28ppm is the solvent peak of eluent PetroChina Company Limited. ether and ethyl acetate respectively.These data show that there is FR-3 in this molecular structure is successfully synthesized.
embodiment 6
The preparation method of the described compound (FR-3) containing multiple active group,
The steps include:
The first step,
(1) 9.30g(0.05mol is taken) cyanuric chloride is dissolved in 80mL acetone, is stirred to and dissolves completely, be slowly warming up to 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(2) under nitrogen protection atmosphere, add and be dissolved in 70mL1, the 6.82g(0.055mol in 4-dioxane) trimethyl phosphite solution, reaction 4h, keeps in reaction process stirring;
(3) after question response terminates, stop insulation, be cooled to room temperature gradually, filter, revolve steaming, obtain intermediate M;
Second step,
(4) by 9.76g(0.04mol) intermediate M is dissolved in 80mL tetrahydrofuran (THF), is stirred to and dissolves completely, be slowly warming up to 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(5) 1.36g(0.01mol is taken) tetramethylolmethane and pyridine be dissolved in 70mL1, and in 4-dioxane, be stirred to and dissolve completely, be added dropwise in the tetrahydrofuran (THF) containing intermediate M, insulation reaction 9h; After having reacted, refrigeration leaves standstill 10h, filters the hydrochloride of acid binding agent, revolves and steams except desolventizing, obtain yellow oily liquid, be the compound containing multiple active group;
The 3g yellow oily liquid that step (5) obtains, with acetone solution, together with being stirred in silica-gel powder etc. quality, normal temperature ventilation is dried, with the ethyl acetate of 1:20 volume ratio and sherwood oil for eluent, carry out silica gel column chromatography separating-purifying, obtain the yellow oily liquid 1.96g after purifying, productive rate is 65.2%.
Claims (3)
1. the compound containing multiple active group, it is characterized in that, its structural formula is:
Or
Or
; In formula: R is-CH
3or-CH
2cH
3.
2. the preparation method of the compound containing multiple active group as claimed in claim 1, is characterized in that,
The steps include:
The first step,
(1) take cyanuric chloride to be dissolved in the first solvent, be stirred to and dissolve completely, be slowly warming up to 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(2) under nitrogen protection atmosphere, add the phosphorous acid ester solution be dissolved in the first solvent, reaction 4 ~ 6h, keep in reaction process stirring;
Described phosphorous acid ester is trimethyl phosphite or triethyl-phosphite;
(3) after question response terminates, stop insulation, be cooled to room temperature gradually, filter, revolve steaming, obtain intermediate M;
Described first solvent is toluene, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane or the mixed solvent of toluene and acetone;
Second step,
(4) intermediate M is dissolved in the second solvent, is stirred to and dissolves completely, be slowly warming up to 40 ~ 60 DEG C, Keep agitation while insulation, reactant is uniformly dispersed;
(5) take polyvalent alcohol and acid binding agent is dissolved in the second solvent, be stirred to and dissolve completely, be added dropwise in the second solvent containing intermediate M, insulation reaction 7 ~ 9h; After having reacted, refrigeration leaves standstill 10h, filters the hydrochloride of acid binding agent, revolves and steams except desolventizing, obtain yellow oily liquid, be the compound containing multiple active group;
Described second solvent is tetrahydrofuran (THF) or Isosorbide-5-Nitrae-dioxane, and polyvalent alcohol is neopentyl glycol, glycerol or tetramethylolmethane, and acid binding agent is triethylamine, diisopropylethylamine or pyridine.
3. the preparation method of the compound containing multiple active group according to claim 2, it is characterized in that, the yellow oily liquid that step (5) obtains, with acetone solution, together with quality is stirred in silica-gel powder, normal temperature ventilation is dried, with the ethyl acetate of 1:20 volume ratio and sherwood oil for eluent, carry out silica gel column chromatography separating-purifying, obtain the yellow oily liquid after purifying.
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| CN110372745B (en) * | 2019-08-07 | 2021-09-07 | 吕梁学院 | Preparation method of flame-retardant compound |
| CN111211350B (en) * | 2020-01-11 | 2023-02-10 | 山东理工大学 | Preparation method of melamine-ring-containing flame-retardant electrolyte easily soluble in organic solvent |
| CN111193067B (en) * | 2020-01-11 | 2022-05-17 | 山东理工大学 | Preparation method of flame-retardant electrolyte for lithium ion battery |
| CN111205322B (en) * | 2020-01-11 | 2022-07-26 | 山东理工大学 | Preparation method of 2,4, 6-trioxo-1, 3, 5-triazine-lithium triphosphate and compound thereof used for flame-retardant electrolyte |
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| CN102634974A (en) * | 2012-03-05 | 2012-08-15 | 中北大学 | Reactive phosphorus triazine flame retardant for dyeing, and preparation method and application thereof |
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